Trifluoroacetic acid → HCID 59547310, compound

HRID 2038574Notes

Reaction equation

HRID 2038574 reaction equation
C([CH:5]1[C@@:9]2([CH2:13][C:12](=[O:14])[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10]2)[CH2:8][C@@H:7]([C:21]([OH:23])=[O:22])[N:6]1[C:24](=[O:39])[C@@H:25]([NH:30][C:31]([O:33][CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:32])[C:26]([CH3:29])([CH3:28])[CH3:27])(C)(C)C.N1CCC[C@H]1C(O)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:34]1([O:33][C:31]([NH:30][C@@H:25]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]([N:6]2[C@H:7]([C:21]([OH:23])=[O:22])[CH2:8][C@@:9]3([CH2:13][C:12](=[O:14])[N:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:10]3)[CH2:5]2)=[O:39])=[O:32])[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86646909HCID 86646909, compound

Product 1

HCID 59547310HCID 59547310, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The protected proline (3S,5R)-tert-butyl-2-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-8-oxo-7-phenyl-2,7-diazaspiro[4.4]nonane-3-carboxylate (H6a) (9.2 mg, 17 μmol) was dissolved in CH2Cl2 (1.0 ml) and treated with trifluoroacetic acid (0.3 ml) for 4 hrs at room temperature. The reaction was concentrated to dryness under high vacuum to give (3S,5R)-2-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-8-oxo-7-phenyl-2,7-diazaspiro[4.4]nonane-3-carboxylic acid (I6a) (17 μmol). The minor diastereomer (3S,5S)-2-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-8-oxo-7-phenyl-2,7-diazaspiro[4.4]nonane-3-carboxylic acid (I6b) (5 μmol) was obtained in similar fashion.

Workup

  1. concentrationThe reaction was concentrated to dryness under high vacuum

Sources & evidence

ORD record
ord-be675f005c634c5686f9f1d500008fc8
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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